470482-43-0

Basic information

• Product Name: (2S,4R)-1-Boc-4-trifluoromethylpyrrolidine-2-methanol
• Synonyms: (2S,4R)-1-Boc-4-trifluoromethylpyrrolidine-2-methanol
• CAS NO: 470482-43-0
• Molecular Formula: C11H18F3NO3
• Molecular Weight: 269.27
• Mol File: 470482-43-0.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (2S,4R)-1-Boc-4-trifluoromethylpyrrolidine-2-methanol(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,4R)-1-Boc-4-trifluoromethylpyrrolidine-2-methanol(470482-43-0)
• EPA Substance Registry System: (2S,4R)-1-Boc-4-trifluoromethylpyrrolidine-2-methanol(470482-43-0)

Safety Data

• Hazardous Substances Data: 470482-43-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(2S,4R)-1-Boc-4-trifluoromethylpyrrolidine-2-methanol is used as an intermediate in the synthesis of various pharmaceuticals. Its unique structure and functional groups make it a valuable building block for the production of a wide range of complex molecules.
Used in Agrochemical Industry:
(2S,4R)-1-Boc-4-trifluoromethylpyrrolidine-2-methanol is also used as an intermediate in the synthesis of various agrochemicals. Its versatility and functional groups allow for the creation of molecules with specific properties for use in agriculture.

Upstream product

• 470482-39-4 (S)-tert-butyl 2-(((tert-butyldimethylsilyl)oxy)methyl)-4-(trifluoromethyl)-2,3-dihydro-1H-pyrrole-1-carboxylate 
• 470482-36-1 (2S)-1-tert-butyl 2-methyl 4-hydroxy-4-(trifluoromethyl)pyrrolidine-1,2-dicarboxylate 
• 102195-80-2 (S)-1-tert-butyl 2-methyl 4-oxopyrrolidine-1,2-dicarboxylate 
• 74844-91-0 1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate 
• 1499-56-5 (R)-4-hydroxy-L-proline ethyl ester 
• 24424-99-5 di-tert-butyl dicarbonate 
• 470482-42-9 (S)-tert-butyl 2-(hydroxymethyl)-4-(trifluoromethyl)-2,3-dihydro-1H-pyrrole-1-carboxylate 

Downstream Products

• 497103-78-3 (2S,4R)-1-tert-butoxycarbonyl-4-(trifluoromethyl)pyrrolidine-2-carboxylic acid 

Relevant articles and documents

Discovery of Pyrrolidine-Containing GPR40 Agonists: Stereochemistry Effects a Change in Binding Mode

A novel series of pyrrolidine-containing GPR40 agonists is described as a potential treatment for type 2 diabetes. The initial pyrrolidine hit was modified by moving the position of the carboxylic acid, a key pharmacophore for GPR40. Addition of a 4-cis-CF3 to the pyrrolidine improves the human GPR40 binding Ki and agonist efficacy. After further optimization, the discovery of a minor enantiomeric impurity with agonist activity led to the finding that enantiomers (R,R)-68 and (S,S)-68 have differential effects on the radioligand used for the binding assay, with (R,R)-68 potentiating the radioligand and (S,S)-68 displacing the radioligand. Compound (R,R)-68 activates both Gq-coupled intracellular Ca2+ flux and Gs-coupled cAMP accumulation. This signaling bias results in a dual mechanism of action for compound (R,R)-68, demonstrating glucose-dependent insulin and GLP-1 secretion in vitro. In vivo, compound (R,R)-68 significantly lowers plasma glucose levels in mice during an oral glucose challenge, encouraging further development of the series.

Influence of 4- or 5-substituents on the pyrrolidine ring of 5-[1-(2-methoxymethylpyrrolidinyl)sulfonyl]isatin derivatives on their inhibitory activities towards caspases-3 and -7 Dedicated to Professor Dr. Ernst-Ulrich Würthwein on the occasion of his 65th birthday

A series of new 4- or 5-substituted pyrrolidine derivatives of 5-[1-(2-methoxymethylpyrrolidinyl)sulfonyl]isatin bearing additional n-butyl or 4-fluorobutyl groups at the isatin nitrogen were prepared and their inhibitory activities have been tested against caspases-3 and -7, which are known to participate in the execution of the programmed cell death, called apoptosis. Several analogues fluorinated at the 4-position of the pyrrolidine ring were also synthesized since such inhibitors might be developed as 18F-radiotracers for molecular imaging of activated caspases in vivo by PET. Enantiomerically pure diastereomeric 4-fluoropyrrolidinyl derivatives inhibited the enzymes in the nanomolar scale, i.e.100-1000 times more efficient than the corresponding 4-methoxy analogues. The 4,4-difluorinated compound showed the best result with IC50 = 362 nM and 178 nM for the aforementioned caspases. In contrast, the 4-methoxy and 4-trifluoromethyl analogues exhibited less inhibition potencies for the enzymes in the μM scale, whereas all 4-OPEG4 (PEG4 = tetraethyleneglycol) and 5-methoxymethyl derivatives were inactive.

Stereoselective synthesis of Boc-protected cis and trans-4-trifluoromethylprolines by asymmetric hydrogenation reactions

Stereocontrolled synthesis of cis and trans-substituted prolines by a divergent approach, leads to the preparation of cis-(4S)- and trans-(4R)-trifluoromethyl-Lproline from hydroxyproline. The key pyrroline intermediates were subjected to hydrogenation (s